Start at the feet and pan up Adam Sandler: the sneakers, the pants that never quite fit, the sloped shoulders, the furrowed brow and world-weary sulk. He's a cartoon man drawn the same in every movie, whether he's in a lonely walk-up or a McMansion crammed with kids. Sandler plays the loser even when his characters have great jobs, hot wives and ideal circumstances. Even then, he simmers with entitlement — he's always one macchiato away from a meltdown.

What's fascinating about Sandler today is how hard he tries to keep from boiling over. In his 20s and early 30s, he elected to play hotheads and morons. Now 48, he's spent the last decade choosing to play a nice guy. Ironically, his “lovable” schlubs are more unnerving. His characters' problems used to stem from their personalities — he was the joke. In films such as his latest, Thomas McCarthy's The Cobbler, where he plays a fourth-generation Manhattan shoe-smith who still lives with his mom (Lynn Cohen), Sandler's the straight man: a victim of a universe that rewards the rich, handsome or cruel, the spokesman for all those sad, self-pitying creeps who claim chicks only like assholes.

Max Simkin is the ultimate Sandler creation: miserable, unappreciated, dateless and too developmentally arrested to do a damned thing about it. When Max was a boy, his father (Dustin Hoffman) ditched the family, leaving Max to run the cobbler shop the Simkins have owned for more than a century. McCarthy and co-screenwriter Paul Sado assume we'll empathize with Max's stuck situation, which is hard. You can root for a 28-year-old who's been handed a raw deal, but 20 years later — and in a high-value New York real estate market — he's guilty of inertia. The Cobbler earnestly buffs out his faults, hoping we won't notice the cracks. But when its virginal bachelor is two years shy of 50, you can't pretend that he just hasn't met the right girl.

One day at the store, Max breaks out a vintage stitching machine that sews soles onto shoes. We know from a prologue that the contraption is magic, a gift from an angel who bestowed it upon Max's ancestor in 1903. To Max's shock, when he kicks off his New Balances and slides into local gangster Ludlow's (Method Man) expensive wingtips, he becomes the crook. Yes, he's literally walking in another man's shoes. But for all its talk about souls and soles, the movie misses the parable's point. Max isn't gaining insight into a person's struggles. He's simply stealing their body to have some fun.

At first, all this is a little sweet. Wearing an Asian man's shoes to stroll through Chinatown, Max is making life more interesting by vacationing at home. Then it gets murky. Max wears the shoes of a rich white man to joyride in his sports car, and the shoes of his handsome white neighbor (Dan Stevens) to see what it's like to feel attractive. It's forgivable wish fulfillment until he enters the apartment of the hot guy he's embodying, watches his model girlfriend take a shower and considers stepping into the water for a shag. He stops himself not because it's date rape but because he'd have to take off his boots and reveal the ruse. Congrats, comedy — you've gone back in time to the Darth Vader costume gag in Revenge of the Nerds, which insisted all nerds deserve a shot at a babe, with or without her informed consent.

The scene rankles because the movie continues to deny that Max is a creep. It's all chipper music and but-he-means-well optimism — the real villain is a real estate developer (Ellen Barkin), whom Max will eventually rouse himself to defeat with the power of shoes. The Cobbler maintains the delusion even when our hero starts committing crimes — walking out on restaurant bills, stealing loafers from a millionaire on the street — in the skin of black men. Once might be a misstep on the part of the filmmakers. Three times, without comment on the pattern, is toxic. The fourth time, Max finally swaps in a white person — a transvestite.

And, in case we forgot (as the film seems to have), Max looks like an actual person who could conceivably be arrested for his bad behavior. By the time he busts into Ludlow's house costumed as a black teenager to rob him of his expensive watch collection (totally justifiable, according to the movie, since Ludlow said something mean about his mom), The Cobbler has invented a new category of terrible: cruel schmaltz. I found myself guiltily hoping that Ludlow's vengeful thugs would attack one of the shoe shop's innocent customers to give Max, and his movie, a conscience. No such bad luck.

A man-child comedian matures at a crawl, kicking and screaming and clinging to what sold seats before. Like Robin Williams before him, Sandler's done hapless romantics, he's done dads, he's done drag. Now it's time to play outright villains in movies braver than The Cobbler, movies that admit the darkness roiling under his smile. Ironically, the closest Sandler's come is when Judd Apatow cast him in Funny People to play, more or less, Adam Sandler. With his charm evaporating more and more with every bad film, he needs to lace up his sneakers, take a long look in a mirror and figure out how to be the best version of the man he's become.

THE COBBLER | Directed by Tom McCarthy | Written by Tom McCarthy and Paul Sado | RLJ Entertainment | Citywide and on-demand

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